


First Date

by claimingsanctuary (timeschange)



Series: Elves and Shipping [2]
Category: Supernatural
Genre: But mostly fluff, Established Relationship, Fluff, Light Smut, M/M, One Shot, Shipper!Sam, and Cuteness, brief Charlie, it's actually way too cute, sort of
Language: English
Status: Completed
Published: 2014-06-23
Updated: 2014-06-23
Packaged: 2018-02-05 21:46:36
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,790
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1833370
Author URL: https://archiveofourown.org/users/timeschange/pseuds/claimingsanctuary
Summary: <blockquote class="userstuff">
              <p>A follow-up fic. Immediately after Dean and Cas finally get together, things are predictably awkward and uncertain, and Sam's tempted to *once again* take drastic measures to get the two together.</p>
            </blockquote>





	First Date

**Author's Note:**

> So this is a follow-up fic to "One Does Not Simply Ship Destiel" (though I guess you could probably read it alone). But I don't recommend that, so here's the link:  
> [One Does Not Simply Ship Destiel](http://archiveofourown.org/works/1416712/chapters/2976253/)  
> I still suck at writing smut, so if you're looking for something that's going to float your boat, this probably isn't it-- it's much more of an adorableness + feels kind of fic. 
> 
> Unbeta'd, because I'm still new to this whole fanfic thing and I'm still not entirely sure what that means.

"Have a nice trip, boys! Drive safely!”

“Thanks, Macy!” Sam called back at the chirpy woman while Dean rolled his eyes so only Cas could see. Cas glanced away, almost smiling. Dean counted it as a win.

“What, Sammy? You’re not gonna ask for her number?” Dean laughed once they were outside.

“Don’t be a dick, man.”

“What, I’m just saying. You’re obviously into her,” Dean teased, tossing his bag in the Impala’s trunk. Sam rolled his eyes and made to get into the car. “Oh, no, buddy—you have lost your shotgun privileges.”

Sam froze with his hand on the door to the passenger seat. “What?” he laughed.

“In the back, Sasquatch. You have caused me  _way_ too much trouble during this hunt. You don’t get to sit in the front seat. Consider it your punishment.”

“You’re not serious,” Sam half-laughed.

“Dead. In the back.”

Cas honest-to-god smirked at Sam as he took the younger Winchester’s seat and Dean laughed at them both, climbing into the car.

“You just want your boyfriend to sit next to you,” Sam grumbled.

“He is  _not_ my—“ Dean began, whirling in his seat, but he broke off with a loud laugh when he saw his little brother trying to find a way to arrange his absurdly oversized legs in the cramped back seat of the Impala.

 

Five minutes into the drive, Cas reached over toward Dean.

Dean jumped a little and glanced at Cas, eyes wide, then back at Sam, who was trying to hide his smirk. All Cas did, though, was take one of Dean’s hands in his own, twining their fingers together.

“Um, Cas…” Dean started when it became clear Cas wasn’t going to say anything. “What are you doing?”

Cas looked at Dean, brows furrowed, as if unsure of what Dean was asking. “I was under the impression that this is what human couples do,” he said uncertainly.

“Cas, we’re not a—“ Dean said, but one glance at Cas shut him up. Cas was staring at him with his customary head tilt, expression confused, worried, and hopeful all at once. “Yeah, Cas. This is what couples do.”

Dean pursed his lips and glanced in the rearview mirror at Sam. Sam, for his part, looked out the window and pretended not to hear. He also pretended not to notice when Dean rearranged their hands to rest more comfortably or when Castiel smiled at Dean like he was the sun of his life. Like there was nothing more he could possibly want in the world so long as he was with Dean.

And if Sam was smiling to himself, well, let’s say he was smiling as the last of Eaton, Wisconsin passed them by. It was, after all, a cute town, and the hunt there definitely provided him with a few days' worth of entertainment.

 

Sam wasn’t sure what he’d expected to come from this whole shipoing/getting-Dean-and-Cas-together thing, but this wasn’t it. He’d expected…well, touching and kissing and public displays of affection, given how much Dean and Cas were prone to wantonly eye fucking in front of everyone. But things seemed to quickly return to normal.

Not in a good way, though. It was all  _suspiciously_  normal. Almost one of Dean’s pretend-this-whole-thing-never-happened normal.

And Sam was not about to let that happen. Not after all the hard work he’d put into this.

“Hey, Cas, you’re going to hang around, right?” Dean asked.

“I have nowhere to be anywhere soon,” Cas said with his peculiar smile. "So...yes, if you'll have me."

"Uh, yeah. Cool.”

But after that, Dean went about business as usual. He took to his laptop for the rest of the afternoon then made Cas watch Star Wars with him later in the evening but he fell asleep on the couch halfway through the Empire Strikes Back.

Cas carried Dean back to his room—both Cas and Sam agreed  _never_ to tell Dean about it—but Cas was back in the living room a minute later.

The next day started similarly. Dean, in a surprisingly good mood, made breakfast, then settled down for another movie. Went back to his computer.

 

Early afternoon, Dean was still sitting at his computer, deep at work.

“Dean,” Castiel’s voice came from behind him. He always forgot how low and beautifully gravelly Castiel’s voice was until he heard it again, and the  _thoughts_  it gave him…

“Cas,” Dean smirked up at him, trying not to seem guilty. The angel craned his neck to see what was on the laptop screen, but Dean shut it before he had the chance. Castiel squinted at the human. “What’s up, man?”

“I was thinking we could…” Cas trailed off, choosing to approach Dean instead of finishing his sentence. Dean stood to meet him, letting Cas get up in his space.

He swallowed audibly when Castiel’s blue eyes roved down his body, pausing at a few choice locations.

“Yeah?” Dean asked, embarrassed by how breathy his voice came out.

Cas didn’t say anything, looking up at Dean through thick lashes with a goddamn  _smirk_ on his face. Cas ducked to press a kiss to Dean’s neck. He snaked his hand underneath Dean’s shirt, running it along Dean’s bare chest, and yeah, maybe Dean squirmed a little, because who would have guessed an angel of the Lord would have such perpetually cold hands.

It was actually a little awkward, a weird sort of groping, but it was also an incredibly Castiel-like move. It’s not like the guy actually knew what he was doing, but if it made him happy Dean was cool with it. And that fact brought a fond smile to Dean’s lips. It also gave him a sort of warm, tingly, feeling in his stomach—completely unrelated to the sexual kind of feeling, but just as nice, he was surprised to find.

“Dean,” Cas breathed, his face only inches from Dean’s. Dean let out a low whine and closed the space between them, unable to hold back any longer.

The kiss was slow and gentle, romantic and the exact sort of thing Dean usually tried to stay far away from. Instead, Dean found himself pulling in closer, sweeping his thumb gently along Castiel’s jaw. He pulled back an inch, just staring into those blue eyes. Cas was smiling at him now, hopeful and happy, his expression reflecting everything Dean was feeling.

For someone who didn’t believe in chick-flick moments, he sure got caught in a helluva lot of them.

That thought is what finally snapped him out of his weird love-coma.

“H’ookay,” Dean said, twisting way out of Castiel’s arms, much as it killed him. “I would  _love_ to do this with you right now, Cas, really, but I was like,  _just_  about to go get some groceries and…stuff, so I’m just gonna, you know…” Dean trailed off, grabbing the Impala keys. “You can come, if you want…?”

Castiel was confused beyond measure, but he assumed that because Dean pulled away so coldly, he wasn’t  _really_ asking Cas to accompany him. If only he knew why. “No. Thank you, Dean.”

Dean walked backward, not taking his eyes off of Cas, as if worried the angel was going to try to follow him, “Awesome. I’ll be back in a bit, we’ll talk later, kay?”

“Okay,” Cas repeated, watching Dean flee.

This made no sense to him. A lot of the things Dean did made no sense to him, but he thought they’d  _finally_ moved on to…something. He didn’t know. But this certainly wasn’t normal behavior, even for Dean.

 

“Sam.”

Sam looked up from his book to see Cas standing uncertainly in the doorway. “Dean’s not here.”

“Yes, I’m aware. I…wanted to speak to you.”

“Oh. Um, everything good on the Dean front?”

“I’m not sure. As you know, the other day Dean and I—“

“No! Ew, no! PG, man. Keep it PG.”

“You’re referring to the rating system you use for movies, I assume. Fine. Dean and I…copulated—“

Sam scrunched up his nose.

“And then he held my hand in the car and while he  _has_ been friendly…”

“And while he has been friendly, what?” Sam prompted after Cas trailed off with a frown.

“When we returned, he went on the computer, and then he fell asleep, and then he watched movies, and then he went back to the computer. It seems he's paying even less attention to me than before, and if I didn't know better, I would have assumed he's upset with me.”

“Did you...say anything? Cuz you know, man, you can sometimes be a bit...” On seeing the worried look Cas was saying, Sam bit his tongue before the word  _rude_ came out. "Frank."

“I didn't say anything to offend him,” Cas said, squinting at Sam like he could stare the answers out of him. "I think he may be avoiding me. Or at least avoiding being alone with me."

“Oh.  _Oh._ You think he’s, like, emotionally shutting down?” Sam clarified. He should have expected this, actually. He’d never met anyone more emotionally constipated than Dean. No way this was all just going to be rainbows and butterflies.

“Perhaps. I don’t know. Dean is…very confusing.”

“Tell me about it,” Sam laughed. “Did  _he_ …um, say anything, or…?”

“I kissed him and he said he had to get groceries.”

“Ew.”

“And he wouldn’t let me see he was doing on his computer.”

“Uh-huh,” Sam nodded automatically, then he seemed to realize what Cas said and backpedaled, “Oh. Really? Um. Yeah, uh, Cas…I hate to break this to you, man, but, uh…Dean only uses his computer for research or for porn, so…”

Cas sat across from Dean, placing his palm flat on the table. “You think he was watching pornography?” he asked, getting, if possible, more confused. “Why? He seemed to enjoy our—“

“Oh, gross,” Sam groaned, “Stop there. I get the point. Look, Dean is—Dean is complicated, you know that. He hasn’t been in a long term relationship since…well, since Lisa, I guess, but you know, he always seriously sucked at it. Like, really bad. He hooks up, and he watches porn, and he denies his feelings. Even when he really likes someone. It’s his thing.”

"You think Dean 'really likes' me?" Cas asked with a small smile.

"I wouldn't have worked so hard to get you two together if I didn't," Sam smiled, running a hand through his hair.

"I see," Cas nodded. He seemed to think something over. “So you don’t think Dean is watching pornography because I wasn’t able to provide Dean with sexual gratification?"

“Wow,” Sam blinked, “Um, first: gross. Second: to be fair, I honestly couldn’t say, but that’s probably not the problem. And I don’t think Dean is exactly, the, uh, leading expert on um…gay sex.” He regretted ever getting involved in this situation in the first place. He regretted it so much. “Just give him time.”

Sam gave Cas a sympathetic smile. This ordeal was frustrating  _him,_ he couldn’t imagine what it must be doing to the angel, who was essentially a baby in a trench coat when it came to understanding his emotions. And friggin’ Dean was tossing the poor guy this way and that, not even realizing what it was doing to him.

“Look, man,” Sam started, rubbing his eyes, “Tell you what. Just…if you’re worried about the porn thing, uh,” he laughed, realizing how awkward this situation was, (not that Castiel had a clue) “I'll give you a tip. You know that stuff I sprayed you with a few days ago? Cinnamon. Dean goes kind of weirdly crazy for the smell. So, um, yeah. You know, have at it. And, uh,” he rubbed at the back of his neck, “have fun. Use protection. Don’t tell me about it afterward.”

Castiel looked thoughtful. “Thank you, Sam.”

“Sure, anytime—“

Cas disappeared with a flutter of wings.

“Yep,” Sam nodded to himself, “nice talking to you, too.”

 

Dean was in a  _good_ mood. He had big plans, and they were going to be awesome. Everything was finally going to be awesome.

He clapped his hands together and grinned.

Yeah, there was no way even Dean Winchester, the fuck-up master, could fuck this up. At least, he was going to try his damnedest not to.

If only he could man up and stop being a sissy. He looked around the bunker’s deserted kitchen, taking a deep breath.  _Just call the freaking angel, idiot._

“Hey, Cas!” he shouted as loud as he could manage, before he could talk himself out of anything, “Mind getting your feathery ass in here? Uh, please?”

Best to get off to a good start. Nice thinking, Winchester.

Cas appeared a second later, his serious face on. Well…you know. More serious than usual.

“Hey, Cas, so...tonight—“

Dean broke off with a sharp intake of breath as Cas shoved him violently onto the counter, lifting him so he was sitting atop it. Cas pressed against him, as close as he possibly could without breaking the fragile human, perched between Dean's legs.

“Cas, what—“ Dean started to ask a question, surprised he was still able to, really, with the onslaught of Cas and hands and lips, but that’s when he breathed in. “You  _son of a bitch._ ”

The angel  _reeked_ of cinnamon. Like, definitely overboard. The dude wasn’t even  _trying_ to be subtle about it. He reached out for Cas, twisting his fingers in the dark hair and pulling the angel to him, not caring just how hard he pulled. Their lips met in a clash of teeth and tongues, and it was accompanied by pulling and pushing and tearing and grinding and biting. It was rough and desperate and forceful, more so than any of their previous kisses, and worlds different from the kiss they shared that morning.

Dean looked forward to discovering the variety of kisses his angel had to offer.

“Cinnamon, Cas?  _Really?_ ” he asked between kisses. “Don’t need it—“ he nipped at the angel’s lip, “—to make me want you—“ moved to his neck, “—you should know that, man.”

The angel hummed into Dean’s mouth, pulling a loud moan from the hunter.

“Dammit, Cas, I wanted to ask you something,” Dean growled, pulling Cas into another violent kiss, clutching at him tightly enough to bruise.

Despite being the one to broach the subject, Dean growled when Cas pulled away to look at him with his big, serious eyes. “I understand if you would still like to watch pornography, Dean, although I  _would_ appreciate it if you would refrain from having sex with other—“

“ _What?_ Cas, what the  _hell_ are you talking about?” Dean demanded. His attention was  _mostly_ fixed on Cas’ words, but with the angel’s heat pressed against his and the smell of cinnamon burning his nostrils, he couldn’t keep his hands, at the very least, from wandering. All over the angel’s body.

“Sam said you only use your laptop for pornography and research, and as you were being secretive, I assumed—“

“That I was watching  _porn_? I wasn’t watching porn, dork, I was looking something up,” Dean chuckled, hopping down from the counter but grabbing at the lapels of Cas’ coat to keep him close, “’Sides, you’re way hotter than any porn star I’ve ever seen,” he smirked, winking at the angel. “’Specially with all those pretty sounds you make.”

“Good,” Cas growled. His hands moved to Dean’s belt, which he undid quickly and efficiently, shoving Dean’s pants down to his knees without any further ado.

“ _Fuck,_ Cas. You can’t just—Sam could walk in any minute—“ Dean glanced at the door nervously, then back at the angel, who was now dropping to his knees. “Oh, no way. Shit, Cas.”

He couldn’t count the number of times he’d fantasized about this. The guy’s lips alone were enough to drive him crazy.

“Sam’s in his room,” Cas assured him, placing one hand on Dean’s hip to hold him in place.

“Do you—“ Dean choked off. The angel looked curiously up at him, then closed his lips around Dean’s dick. “ _Shit. Doyouevenknowhatyou’redoing_?” He asked in a rush.

“Not really,” Castiel admitted, speaking around Dean’s cock. His tongue flicked out experimentally. “It tastes…very much like  _you._ Interesting. Not unpleasant.”

Dean snorted, but couldn’t do anything more than thread his fingers through Cas’ dark hair, making it stick up in every direction. Cas hummed, rubbing his thumb in circles across Dean’s hip.

“ _Cas,_ ” Dean groaned as the vibration shot through him, head slamming back into a cupboard. He was about to make another quip when Cas sank lower, his pink lips parting to accommodate Dean’s size.

Cas took to the whole thing like a natural. His tongue was definitely magical, and it helped that the angel didn’t seem to have a gag reflex.

“Shit, I was gonna—“ Dean panted, eyelids fluttering, “Was gonna ask you something—yeah, oh God—I wanted to ask you something, babe.” Cas hummed again, making Dean throw his head back and slam a palm down on the counter. It was a while before he could speak again. “I was gonna make it romantic.”

Cas pulled off with a pop, looking up at Dean with a head tilt. “What?”

“Jesus  _fucking_ Christ, Cas, you don’t just fucking  _stop,_ ” Dean growled.

“What were you going to tell me?” Cas asked, refusing to be swayed.

“A date, Cas. I was going to ask you out on a date, happy?” Dean growled.

“Really?” Cas asked, an excited smile spreading across his face. He looked a tad crazy, with his uncharacteristic grin, flushed cheeks, and tufts of dark hair sticking up this way and that. He rose to his feet, despite Dean’s exasperated groan. “A...date?”

“Are you really just—dammit. Yeah, Cas. That’s what I was looking up earlier. I wanted to take you out somewhere official, but it would be stupid to take you to a restaurant, seeing as you don’t need to eat, so, I was trying to find something else awesome nearby we could do instead, and I definitely  _wasn’t_ going to do any of  _this_  kinda stuff until  _after_ , but you brought it on yourself with the fucking cinnamon, so  _come the hell with me_ ,” Dean growled, pulling up his jeans and dragging Cas across the bunker to his room.

Cas followed him readily, like an eager puppy.

Once inside the room, Dean pulled Cas to him, kissing every inch of Cas’ skin that was available to him. It wasn’t enough, so he quickly tried to remedy the situation, tearing off Cas’ clothing like they were causing him personal offense. “Not gonna magic my clothes off this time?” he mumbled into Castiel’s neck.

“I believe you,  _ah_ ,” Cas’ breath hitched when Dean nipped at his shoulder, “showed me the value of... _Dean, yes_ …doing it...slowly. Last time.”

“Damn right, I did,” Dean growled possessively, shoving Cas back onto the mattress once the angel was divested of his clothing. His bed was going to smell like Cas and cinnamon for weeks. Although, it was hopefully going to smell like Cas for much longer than that. Forever, if he had his way. “But it's okay to get a little overexcited sometimes.”

Dean lost the rest of his clothes and climbed hover over Castiel on the bed.

Cas ran his hands across the planes of his chest, tracing Dean’s anti-possession tattoo with awe written across his face. “Dean,” he breathed.

“Yeah, Cas,” Dean leaned in to pull Cas into a deep kiss. When he tried to pull away, Cas didn’t let him, instead rolling so he was on top. Dean let out a breathy laugh, grinding up into Cas.

Cas let out a nigh-pornographic moan and reached over toward Dean’s bag, still unpacked from the hunt in Eaton. He came back with the bottle of lube, popping the cap and squeezing a generous amount into his palm.

“Look at you, taking charge,” Dean smirked up at him. He ran his hand down Cas’ back, cupping his ass and guiding Cas to grind into him.  Cas ducked his head and started planting kisses along Dean’s collarbone. “I like it,” the hunter breathed.

Cas lowered his slicked-up hand, pausing to pump Dean’s dick a few times and leaving the hunter writing and breathless, and then brought his hand lower.

Dean wasn’t expecting to feel Cas’ fingers pushing his legs open.

“Woah, Cas!” Dean panicked, jerking away, “No, we don’t—I mean, you’re the— I can’t—“

“It’s not customary to switch off?” Cas said, giving Dean his sad, tilted-head look even as he straddled the human. He pouted a little, and it was the cutest fucking thing Dean had ever seen. And hell if he could ever deny that face. He nodded breathlessly, shutting his eyes.

“Uh, no, Cas, it’s good. You just…caught me off guard. If you want, we can…whatever you want.”

Cas gave Dean a small smile, leaning in to press a chaste kiss to Dean’s lips. “Thank you, Dean.”

“Just—go slow. And gentle. More gentle than I was with you, cuz you’re an angel and I’m, heh, fragile, and—“

“Dean.” And that was all it took to shut Dean up. “I have you.”

He jumped and squirmed and tensed up at the first intrusion of Castiel’s finger, and it took a showering of kisses and soothing words before Cas got him to relax again.

But once Dean got over the weirdness of it-- and the thought that,  _no,_ this wasn't anything weird, they just...switched off, right? Normal. He could enjoy either way and it had no effect on his masculinity whatsoever, right? Anyways, once he got over those thoughts, it was awesome, and Dean had no regrets. 

Cas made surprisingly quick work of opening him up, and a small part of Dean wondered if Cas was using some sort of weird angel healing mojo on him, to make it feel better or something (because no way in hell it just felt this good, right? Like, normally? Because if so, why had he even  _bothered_ with chicks?), but at this point, he didn’t even care.

Because he’d never felt anything like this before, and he was sure he’d never feel it gain.

“Talk to me, Dean,” Cas growled, trailing kisses down Dean’s chest. His lips closed around Dean’s cock again, even while his fingers worked to open Dean up. "I want to hear you."

“Fuck, Cas,” Dean groaned, arching off the bed and twisting his hands into the sheets. “Feels so good. Shit. Cas, please, Jesus fucking--”

Cas slipped in a third finger.

“ _Fuckshitmotherfuckinghell,_ ” Dean shouted when Cas hit his prostate, “Fuck! Do that again. Now.”

Cas chuckled into Dean’s abdomen. “You  _do_ realize these walls are thin and you have a brother with a room not far from here,” Cas admonished.

“He can turn on music if he doesn’t like it,” Dean growled, grabbing Cas’ hair and pulling him up to his lips. The smell of cinnamon flooded his nostrils. “I’m ready, man. Do your worst,” Dean smirked, partially to hide his nerves.

“You're...ready for me to penetrate you now?” Cas asked, looking at Dean from underneath hooded eyes.

Dean laughed. He was in the middle of having hot, weird, gay, human-on-angel sex, and he was laughing. “Don’t ever change, Cas.”

“I won’t,” Cas smiled, not even entirely sure what he’d said to make Dean laugh.

“You go right ahead and penetrate me, baby,” Dean laughed again, kissing Cas.

That was all the encouragement Cas needed, and it’s like a pair of floodgates were opened, and a millennia of Castiel’s repressed sexual energy came pouring out.

Cas hit Dean’s prostate on the very first thrust, sending Dean practically flying off the mattress in a flurry of curses and groans. Raking his fingernails up and down Cas’ back, Dean brought just as many delicious noises from the angel’s lips.

“Lemme— _fuck—_ give me more of that angelic dirty talk, Cas,” Dean said, wrapping his legs up around Cas’ hips to give him a better angle. “Holy Mother of—“

“I won’t give you anything if you— _oh, Dean_ _—_ keep blaspheming.”

“Talk dirty to me, angel boy,” Dean growled. He pushed up to meet Castiel’s thrusts, and soon they’d both moved well past the realm of being able to speak.

“Cas,” Dean pled, kissing Castiel’s lips, his jaw, his left eye, and back to his mouth. “I’m close, Cas. I need—“

“I know,” Cas said into Dean’s lips, reaching a hand between them to stroke Dean. The human whined beneath him, thrusting up into Cas’ hand. “You're beautiful."

" _Cas,"_ Dean whined, digging his nails into the angel's back. "Love you, Cas," he breathed, kissing Castiel before he could regret anything.

"I love you too, Dean Winchester.”

Dean came shouting Cas' name.

 

"Jesus,” Dean breathed, blinking up at the ceiling.

“Dean,” Cas growled into his neck, moving just slightly so his wild black hair tickled just beneath Dean’s jaw.

“Right, sorry, sorry, no blaspheming during sex. I got it."

"That was...very pleasurable."

Dean hummed in agreement. "Hey, what time does that alarm clock say it is?”

Cas grumbled, lifting himself off Dean to look at the clock. “Four fifty.”

“Shit. Up, Cas. Get dressed, we have a date to get to.”

“Where are we going?”

“There’s a carnival a couple cities over,” Dean beamed at him. “You’re going to love it, man.”

“I don’t know what that is,” Cas frowned.

"Fun. Food. Games. Rides. It’s like the center of our culture, dude.”

“I’m not sure that’s accurate.”

 

Sam looked up when he heard Dean’s voice down the hallway. Dean was explaining something in a low voice, obviously excited. Maybe they’d kissed and made up, then.

"Hey. You guys going somewhere?” he asked with furrowed eyebrows when Dean and Cas entered the room.

"Yep,” Dean beamed at him. The expression "he was practically glowing" came to Sam's mind. And that was new.

"We're going on a date,” Cas supplied, casting a loving glance at Dean.

Dean blushed, but he didn’t say anything at Sam’s shocked look.

“ _Really_?” the younger Winchester asked, smiling now.

“Yeah, I’d invite you too, Sam, but first, there’s gonna be clowns, and second—I just don’t want you to come.”

“I would've passed anyway, jerk. But have fun. Seriously. And I’m happy for you two.”

“Yeah, yeah,” Dean grumbled, grabbing his jacket off the hook and leading Cas out the door.

The second they were gone, Sam pulled out his phone.

“Miss me already?” Charlie asked, diving straight into the conversation.

“Yeah, that was it,” Sam rolled his eyes. “That, and, I have some  _developments_ on our, uh, Operation Destiel.”

“Wait, really? Because last I heard, Cas was still pissed about his little eavesdropping problem.”

“Yeah, I was waiting to tell you till I had more to share, but…when I got back from driving you to the airport, they were kind of locked in Dean’s room.”

“ _They were not!”_

“Yeah. And they just left for a date.”

“Are you messing with me, Winchester? Because if so, you’re playing a dangerous game. You don’t mess with a girl’s OTP.”

“I don’t know what that means,” Sam laughed, “But I’m serious. I just thought you’d like to know.”

“Hells yeah, I’d like to know. You keep updating me on this, and don’t you dare hold back.”

“Yeah, sure, Charlie. But I’m not giving you any weird details or anything,” he said, tucking a lock of hair behind his ear. “I’m just glad they can both be happy.”

 

Dean learned several things on his date. First, he learned that he had no idea how to do dates. Second, he learned that it was okay be awkward because Cas was a million times more awkward. Third, he loved it.

Fourth, Cas was terrible at ski ball and he  _loved_ ferris wheels. His face lit up when the wheel stopped at the top, and he pointed out to Dean everything he saw, even though Dean was right up there with him and had two eyes to see for himself. Fifth, Cas took to cotton candy like he’d taken to cheeseburgers. Sixth, the angel loved it when Dean did the cliche-romance-movie-thing where he won Cas a stuffed animal. (It was a shooting game. Dean happened to be very good). Seventh, those warped mirrors in "The House of Mirrors" made both of them laugh harder than either could remember laughing before.

Eighth, and most importantly, Dean learned that this was his last first date ever, because nothing in this world or the next was ever going to make him give Castiel up.

And this time, Dean told Cas exactly that.

**Author's Note:**

> Don't forget to leave a comment letting me know what you thought! Or, even better, [GO FOLLOW ME ON TUMBLR](http://fantasy-novelist.tumblr.com/) and shoot me a message telling me what you thought! (Or just talk to me about normal stuff, because I'm always open to making new friends)
> 
> Anyway, thanks for reading! Hope you enjoyed!


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